Comparative analyses constitute an important complement to studies of adaptive behavior. Previous studies of avian mating systems considered the role of paternal care and habitat type on the evolution of polygyny. We extended those studies and included in our analyses the role of habitat quality, as characterized by food supply. Species in the monophyletic lineage of acrocephaline warblers (Acrocephalus, Chloropeta, Hippolais) are widely distributed, inhabit a variety of different habitats, and show a variety of breeding systems. We present a phylogenetic analysis of parental care and mating system characteristics in relation to ecological traits in 17 species. On the basis of a molecular phylogeny, we reconstructed patterns of changes from social monogamy to polygyny, and in paternal brood care. Specifically, we analyze the coevolution of brood care participation of males and social system, and how it relates to habitat quality. Furthermore, we assessed the phylogenetic inertia of mating systems. We found support for the hypothesis that change to highly productive habitats was associated with a greater emancipation of males from brood care, and with polygyny and promiscuity. Poor habitats, on the other hand, were associated with monogamy and the occurrence of helpers. In contrast to some morphological characters, mating systems appear to be phylogenetically labile.